Samantha Grace needs to punish her slave for not obeying her rules so she made a few changes in his daily routine. She will dress him up in some girly clothes just so he can be more attractive to his future fucking buddies.
 
I can see the cum stains on your panties. What did I tell you about that? Now, I have a new punishment. Obviously, you cannot be trusted with panties because you are going to cum-stain them so I think I am going to have to put you in a pair of yoga pants, like mine. You will have to wear these pants so you don't get any jizz on your panties. Would you feel nice in a tight pair of pants? In addition to this, I will put you in a nice bra as well.
 
The other aspect of your punishment for being a dirty boy will be a nightly ass pounding. You are going to be fucked up your butt every night by a different person. I will turn you into a slutty girl who is going to be drilled by horny men. It is time for you to get ready because we are starting tonight.
 
- Samantha Grace
 

 
Kendra here is going to teach you a thing or two about being feminine and taking dick. She's a pretty hot tranny that gets fucked in the ass daily by big, hung studs.
 
I'm so glad that you're looking to come on this journey with me. I have to tell you now that as a transsexual, I love nothing more than being as girly as possible for my lover. It's usually big muscly men that get to play with me. I love how it feels to have my asshole fucked by their massive dicks. You've never felt anything until it's a big cock in your tight feminine asshole.
 
Do you like the idea of being a sissy bitch and taking it in the ass? I think with a little work you could pull off being a woman and find a man that was more than willing to hump and dump you. You strike me as the type of sissy that would accept any cock no matter who it came from. You are one dirty feminine slut - I can't wait to hear about your first dicking!
 
- Kendra
 

 
Jade Indica has put a lot of thought into her sissy boy's outfit for the big date. But since the fellow does not understand the severity of the situation while the hot brunette is instructing him she will need to use a chastity device to control the man's urges.
 
I have been waiting for you. It is not nice to be late. If you want to be a real chick, you need to be punctual. Now it is time for you to put your girl clothes on. Your date is going to be here soon so we have some time to prepare you for what is going to happen tonight.
 
Are you ready to put on these pink dresses? We need to choose the best one for you. I am going to choose the cutes outfit for you since I want you to be the prettiest lady. Look at that cock, it is getting hard. This is really turning you on. I like the fact that you are getting horny while trying on women's clothes. I might have to throw you chastity just to control you since I don't want any precum stains on these gorgeous outfits. I know you are excited to get into my attire and to smell like me.
 
- Jade Indica
 

 
Miss Medina is destined to make sure that you fully embrace the fact that you're a sissy. She's got an outfit for you today - go and try it on!
 
Slave boy, come over here! I got you some nice stuff today from the shops. Let's start off with this pink top - I think it looks absolutely fantastic, and I'm so looking forward to having your sissy ass in it! Oh, before you slip it on, get naked and start with the thong. That has to be the first thing that I see the feminine you wearing.
 
Wow, that's just absolutely fantastic. I never knew that you'd be such a great transvestite! All that's required now is for you to get these high heels around your feet and we're set to go. Oh, this dildo? Don't worry about that for now. I'll introduce you to this guy once we're doing with the makeup. I think you're going to like what I have planned for your feminine ass though.
 
- Chi Chi Medina
 

 
Training for sissy boys like you is really important. Mandy Candy knows this, and is planning to teach you the ways of enjoying big black cock.
 
What we're going to do today is give you a nice lesson in enjoying big black cock. I picked up this dildo a few days ago with training you in mind, and to be honest, it's just perfect for the job. You'll find that the entire length of this thing is about a foot, so you've got 12 inches of pure big black bliss to enjoy - think you can handle it?
 
I know it's hard at first, but you do want to be a good sissy, right? Well this is all part of the experience, because a girl's best asset is her ability to suck and fuck dudes that have massive pieces of meat between their legs. Come on now, the ultimate fantasy of any sissy bitch is to get nailed in the ass by a huge ebony dick - let's get you trained for it!
 
- Mandy Candy
 

 
Tabitha and Jessica know how to doll up a man into a pretty girly chick. They are great at choosing an outfit for a lucky guy who will be the center of their amazing party.
 
We are going to dress you up in a little bra and a cute short skirt so you can show off your bootie. You are also going to wear a tiny thong. I think he will need some makeup as well since we don't want him walking around like this. Some bright red lipstick will look amazing on you and, of course, we cannot forget the eye shadow.
 
After we are finished with dolling you up we are going to have a great party and invite all of our friends. Our girlfriends are probably going to laugh at you since we are going to show you off to everyone. But that is not where the fun ends. There are going to be some gay guys at the party because they are always up for some dick sucking. This is where you come in since you will have a lot of cocks to suck. It is going to be a long night.
 
- Tabitha & Jessica
 

 
Mistress Selena has some sexy lingerie for you to try on today. Head into her chamber now and see what she has in store for your sissy ass.
 
I know how much you love being a sissy, so I thought today would be a really good time to see just how far your fetish goes. How about we start with your pansy little ass getting dressed up in these knickers for me? Do you think that would be a good idea? Just look at how frilly they are - you're going to look like such a little slut in these!
 
I can tell you now, these guys at the party tonight are going to have their way with your hot ass. Once I'm finished dressing you up like the little slut you so desperately want to be, they'll be no stopping that cute little butt of yours from being fucked by a big cock. Tell me now, just how many loads can your feminized ass take from alpha males that are going to fuck the shit out of you?
 
- Mistress Selena